title: Study of physicochemical interaction of aryloxyaminopropanol derivatives with teicoplanin and vancomycin phases in view of quantitative structure-property relationship studies.
abstract: The aim of this work was to study the physicochemical interactions between chiral stationary phases and chiral molecules and to elucidate which of the specific interactions are more or less important. The HPLC separation of 58 aryloxyaminopropanols was performed on two chiral stationary phases containing the macrocyclic antibiotics teicoplanin or vancomycin and using a methanol/acetonitrile/acetic acid/triethylamine mobile phase (volume ratios 45/55/0.3/0.2). The resolution of enantiomers (Rij) as the target variable was predicted for the mentioned kind of compounds by means of thoroughly selected descriptors provided by the applied Dragon software. The created QSPR models can be considered as a way to explore and discover new relationships or interactions between the quantitative structure and resolution of enantiomers. For calculation and validation of the QSPR models, different modelling methodologies were applied based on MLR (multiple linear regression) and ANN (artificial neural network) techniques. Both methods exhibit an ability for successful prediction of the enantioresolution characteristics of the studied molecules. The results seem to demonstrate that it is possible to predict resolution values of enantiomeric separations of related compounds on given chromatographic systems.
authors.affiliation: Department of Chemistry, Faculty of Natural Sciences, University of Ss. Cyril and Methodius, Nám. J. Herdu 2, SK-917 01 Trnava, Slovakia. katarina.boronova@ucm.sk
authors.forename: Katarína
authors.initials: K
authors.lastname: Boronová
authors.forename: Jozef
authors.initials: J
authors.lastname: Lehotay
authors.forename: Katarína
authors.initials: K
authors.lastname: Hroboňová
authors.forename: Daniel W
authors.initials: DW
authors.lastname: Armstrong
mesh_terms: D000704:Analysis of Variance; D001185:Artificial Intelligence; D002851:Chromatography, High Pressure Liquid; D016014:Linear Models; D009682:Magnetic Resonance Spectroscopy; D008970:Molecular Weight; D025341:Principal Component Analysis; D011412:Propanolamines / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship; D015203:Reproducibility of Results; D012984:Software; D012995:Solubility; D013237:Stereoisomerism; D017334:Teicoplanin / Q000737:chemistry*; D014640:Vancomycin / Q000737:chemistry*
chemical_list: D011412:Propanolamines; D017334:Teicoplanin; D014640:Vancomycin
keywords: Artificial neural network; Aryloxyaminopropanol derivatives; Quantitative structure–property relationship; Resolution of enantiomers; Teicoplanin; Vancomycin